Triphenylamine type organic hole transport material with 1,1'-bi-2-naphthylamine as parent nucleus and synthesis and application of triphenylamine type organic hole transport material

A hole transport material, binaphthylamine technology, applied in the field of synthesis of triphenylamine organic small molecules, to achieve the effect of reducing the recombination of electrons, high yield and good shape stability

Active Publication Date: 2019-10-25
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few studies on the application of triphenylamine organic small molecules with binaphthylamine as the core in perovskite solar cells.

Method used

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  • Triphenylamine type organic hole transport material with 1,1'-bi-2-naphthylamine as parent nucleus and synthesis and application of triphenylamine type organic hole transport material
  • Triphenylamine type organic hole transport material with 1,1'-bi-2-naphthylamine as parent nucleus and synthesis and application of triphenylamine type organic hole transport material
  • Triphenylamine type organic hole transport material with 1,1'-bi-2-naphthylamine as parent nucleus and synthesis and application of triphenylamine type organic hole transport material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthetic route of triphenylamine organic small molecule 3 with binaphthylamine as the core:

[0034]

[0035] In a 100mL two-necked flask, add 0.417g 6,6'-dibromo-[1,1'-binaphthyl]-2,2'-diamine 1, 1.059g triphenylamine borate 2, 0.054g tetra (Triphenylphosphine)palladium, 15ml tetrahydrofuran (THF), stirred for 5 minutes under nitrogen protection. Subsequently, the prepared sodium carbonate solution (8 mL of water + 0.400 g of anhydrous sodium carbonate powder) was added to the mixture. The resulting solution was stirred at reflux for 20 hours under nitrogen protection. After cooling, the solvent was distilled off under reduced pressure. The crude product was extracted, separated and dried, and finally separated by column chromatography (eluent: petroleum ether / ethyl acetate=2 / 1) to obtain 0.267 mg of 6,6'-bis(4-(bis(4- Methoxyphenyl)amino)benzene)-[1,1'-binaphthyl]-2,2'-diamine 3, yield 64%. 1 H NMR (400MHz, d 6 -DMSO)δ(ppm): 7.97(s, 2H), 7.82(d, J=9.16Hz, 2H)...

Embodiment 2

[0037] Synthetic route of triphenylamine organic small molecule 5 with binaphthylamine as the core:

[0038]

[0039] In a 100mL two-necked bottle, add 0.540g 6,6'-dibromo-N 2 ,N 2 ,N 2’ ,N 2’ -Tetramethyl-[1,1'-binaphthyl]-2,2'-diamine 4, 1.216g triphenylamine borate 2, 0.054g tetrakis(triphenylphosphine)palladium, 15mL tetrahydrofuran (THF) , and stirred for 5 minutes under nitrogen protection. Subsequently, the prepared sodium carbonate solution (8 mL of water + 0.400 g of anhydrous sodium carbonate powder) was added to the mixture. The resulting solution was stirred at reflux for 20 hours under nitrogen protection. After cooling, the solvent was distilled off under reduced pressure. The crude product was extracted, separated and dried, and finally separated by column chromatography (eluent: petroleum ether / ethyl acetate=5 / 1) to obtain 0.270 mg of 6,6'-bis(4-(bis(4- Methoxyphenyl)amino)benzene)-N 2 ,N 2 ,N 2’ ,N 2’ -Tetramethyl-[1,1'-binaphthyl]-2,2'-diamine 5, ...

Embodiment 3

[0041] Synthesis of triphenylamine organic small molecule 6 with binaphthylamine as the core:

[0042]

[0043] In a 100mL two-necked bottle, add 0.300g 6,6'-bis(4-(bis(4-methoxyphenyl)amino)benzene)-[1,1'-binaphthyl]-2,2'- Diamine 3, 0.237g 4-iodoanisole, 0.00156g tris(dibenzylideneacetone)dipalladium, 0.00241g 2-cyclohexylphosphine-2',4',6'-triisopropylbiphenyl, 0.115g potassium tert-butoxide and 10mL tert-butanol were heated and stirred at 95°C for 30 hours under the protection of nitrogen. After cooling, the solvent was distilled off under reduced pressure. The crude product was extracted, separated and dried, and finally separated by column chromatography (eluent: petroleum ether / ethyl acetate=1 / 1) to obtain 0.219g 6,6'-bis(4-(bis(4- Methoxyphenyl)amino)benzene)-N 2 ,N 2’ -Bis(4-methoxyphenyl)-[1,1'-binaphthyl]-2,2'-diamine 6, yield 73%. 1 H NMR (400MHz, d 6 -DMSO) δ (ppm): 8.05 (s, 2H), 7.91 (d, J = 10.80Hz, 2H), 7.54 (d, J = 7.20Hz, 4H), 7.45 (t, J 1 =8.64Hz,J...

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Abstract

The invention relates to a triphenylamine type organic hole transport material with 1,1'-bi-2-naphthylamine as a parent nucleus and synthesis and application of the triphenylamine type organic hole transport material. The compound adopts triarylamine as an electron-donating unit, and the 1,1'-bi-2-naphthylamine with a certain helix structure is used as the parent nucleus. The compound has a structural formula (I) shown in a formula I (please see the description for the formula), wherein R1 is C1-C12 hydrocarbyl and C1-C12 alkoxy. R2 and R3 are aromatic ring groups containing N, S or O substituted C4-C20, or C1-C20 hydrocarbyl, or hydrogen atoms. The compounds can be used as hole transport materials in perovskite solar cells and have the ability of hole transport. The molecule has a C2 symmetry axis, and the prepared hole film has good morphological stability, so that the charge recombination caused by film defects is effectively reduced, and effective hole transfer in the molecule canbe produced. The triphenylamine type organic hole transport material has characteristics of simple synthesis, simple process, outstanding photoelectric performance, high hole mobility of hole molecules and good photothermal stability.

Description

technical field [0001] The invention relates to a triphenylamine compound and its application, in particular to the synthesis and application of a triphenylamine organic small molecule with binaphthylamine as the core. Background technique [0002] Against the background of energy crisis and environmental pollution, solar energy, as a clean and renewable energy source, is gradually entering human life. Among them, solar cells are one of the main technologies for utilizing solar energy. Perovskite solar cells (JACS, 2009, 131(17): 6050.). Since its inception, it has shown strong commercial application prospects due to its advantages of high efficiency, low cost, low energy consumption, and easy preparation. [0003] At present, perovskite solar cells are classified according to structure, mainly divided into positive perovskite solar cells and reverse perovskite solar cells, in which the electron transport layer and hole transport layer of the latter are made of organic com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/92C07C213/08H01L51/42H01L51/46
CPCC07C217/92C07C213/08H10K85/626H10K85/633H10K85/615H10K30/00Y02E10/549
Inventor 路雨宗雪平崔天强盖鸿玮薛松
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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